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DE1163274T1 - METHOD FOR CROSSLINKING HYALURONIC ACID WITH POLYMERS - Google Patents

METHOD FOR CROSSLINKING HYALURONIC ACID WITH POLYMERS

Info

Publication number
DE1163274T1
DE1163274T1 DE1163274T DE00901772T DE1163274T1 DE 1163274 T1 DE1163274 T1 DE 1163274T1 DE 1163274 T DE1163274 T DE 1163274T DE 00901772 T DE00901772 T DE 00901772T DE 1163274 T1 DE1163274 T1 DE 1163274T1
Authority
DE
Germany
Prior art keywords
cross
linked
polymer
process according
ether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DE1163274T
Other languages
German (de)
Inventor
Catherine Alexander
Jane Elizabeth Fraser
Xiaobin Zhao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mentor Biopolymers Ltd
Original Assignee
Vitrolife UK Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Vitrolife UK Ltd filed Critical Vitrolife UK Ltd
Publication of DE1163274T1 publication Critical patent/DE1163274T1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/28—Polysaccharides or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/20—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Materials Engineering (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Hematology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Polymers & Plastics (AREA)
  • Birds (AREA)
  • Ophthalmology & Optometry (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Materials For Medical Uses (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Iron Core Of Rotating Electric Machines (AREA)
  • Glass Compositions (AREA)
  • Cosmetics (AREA)

Abstract

The present invention provides a process for the production of hyaluronic acid (HA) derivatives cross-linked with another polymer, in particular multiple e.g. double cross-linked hyaluronic acid derivatives. The invention also provides novel cross-linked derivatives, products containing them and their uses in cosmetic, medical and pharmaceutical applications.

Claims (27)

00 901772,4 : :··:· *: :: ; ·: j .· Vitrolife UK Ltd ■·■· · . - «. .. »I.« /1 Ansprüche00 901772,4 : :··:· *: :: ; ·: j .· Vitrolife UK Ltd ■·■· · . - «. .. »I.« /1 Claims 1. Verfahren zur Herstellung von mehrfach quervernetzten Derivaten der Hyaluronsäure, wobei das Verfahren die Quervernetzung von HA mit einem oder mehreren von HA verschiedenen Polymeren und wahlweise mit einem anderen HA-Molekül über zwei oder mehr unterschiedliche funktioneile Gruppen umfasst.1. A process for producing multiply cross-linked derivatives of hyaluronic acid, wherein the process comprises cross-linking HA with one or more polymers other than HA and optionally with another HA molecule via two or more different functional groups. 2. Verfahren gemäß Anspruch 1, wobei das besagte Polymer unter einem Biopolymer oder einem synthetischen Polymer ausgewählt ist.2. Process according to claim 1, wherein said polymer is selected from a biopolymer or a synthetic polymer. 3. Verfahren gemäß Anspruch 1 oder Anspruch 2, wobei das besagte synthetische Polymer unter Polyvinylalkohol (PVA), Polyethylenoxid (PEO) und Polypropylenoxid (PPO) sowie unter Copolymeren von irgendeinem der zuvor erwähnten Polymere, Polyacrylsäure, Polyacrylamid und von anderen Hydroxyl-, Carboxyl- und hydrophilen synthetischen Polymeren ausgewählt ist.3. A process according to claim 1 or claim 2, wherein said synthetic polymer is selected from polyvinyl alcohol (PVA), polyethylene oxide (PEO) and polypropylene oxide (PPO), as well as copolymers of any of the aforementioned polymers, polyacrylic acid, polyacrylamide and other hydroxyl, carboxylic and hydrophilic synthetic polymers. 4. Verfahren gemäß Anspruch 1 oder Anspruch 2, wobei das besagte Biopolymer unter Polypeptiden, Cellulose und ihren Derivaten, wie Hydroxyethylcellulose und Carboxymethylcellulose, Alginat, Chitosan, einem Lipid, Dextran, Stärke, Gellangummi und anderen Polysacchariden ausgewählt ist.4. A method according to claim 1 or claim 2, wherein said biopolymer is selected from polypeptides, cellulose and its derivatives such as hydroxyethylcellulose and carboxymethylcellulose, alginate, chitosan, a lipid, dextran, starch, gellan gum and other polysaccharides. 5. Verfahren gemäß einem der Ansprüche 1 bis 4, wobei die funktionellen Gruppen unter Hydroxyl, Carboxyl und Amino ausgewählt sind.5. Process according to one of claims 1 to 4, wherein the functional groups are selected from hydroxyl, carboxyl and amino. 6. Verfahren gemäß einem der Ansprüche 1 bis 5, wobei die Quervernetzung mittels zwei oder mehr unterschiedlicher Bindungen, gewählt unter Ether-, Ester-, Sulfon-, Amin-, Imino- und Amidbindungen, bewirkt wird.6. A process according to any one of claims 1 to 5, wherein the cross-linking is effected by means of two or more different bonds selected from ether, ester, sulfone, amine, imino and amide bonds. 7. Verfahren gemäß einem der Ansprüche 1 bis 6, wobei das Quervernetzungsmittel unter Formaldehyd, Glutaraldehyd, Divinylsulfon, einem Polyanhydrid, einem Polyaldehyd, einem mehrwertigen Alkohol, einem Carbodiimid, einem Epichlorhydrin, Ethylenglykol,7. The method according to any one of claims 1 to 6, wherein the crosslinking agent is selected from formaldehyde, glutaraldehyde, divinylsulfone, a polyanhydride, a polyaldehyde, a polyhydric alcohol, a carbodiimide, an epichlorohydrin, ethylene glycol, §0 901772.4§0 901772.4 Vitrolife UK LtdVitrolife UK Ltd 1 DE/EP 1 1 63274T1 1 EN/EP 1 1 63274T1 Butandioldiglycidylether, Diglydidylether, Polyglycerinpolyglycidylether, Polyethylenglycoldiglycidylether, Polypropylen-glycoldiglycidylether oder einem Bis- oder Polyepoxy-Quervernetzungsmittel ausgewählt ist.butanediol diglycidyl ether, diglydidyl ether, polyglycerol polyglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether or a bis- or polyepoxy crosslinking agent. 8. Verfahren gemäß einem der Ansprüche 1 bis 7, wobei eine Etherbindung unter Verwendung eines Quervernetzungsmittels, gewählt unter Bis- und Polyepoxide^ unter alkalischen Bedingungen gebildet wird.8. A process according to any one of claims 1 to 7, wherein an ether bond is formed using a crosslinking agent selected from bis- and polyepoxides^ under alkaline conditions. 9. Verfahren gemäß einem der Ansprüche 1 bis 7, wobei eine Esterbindung unter Verwendung eines Quervernetzungsmittels, gewählt unter Bis- und Polyepoxiden, unter sauren Bedingungen gebildet wird.9. A process according to any one of claims 1 to 7, wherein an ester bond is formed using a crosslinking agent selected from bis- and polyepoxides under acidic conditions. 10. Verfahren gemäß Anspruch 8 oder Anspruch 9, wobei das Quervemetzungsmittel unter 1,2,3,4-Diepoxybutan und 1,2,7,8-Diepoxyoctan ausgewählt ist.10. A process according to claim 8 or claim 9, wherein the crosslinking agent is selected from 1,2,3,4-diepoxybutane and 1,2,7,8-diepoxyoctane. 11. Verfahren gemäß einem der Ansprüche 1 bis 7, wobei eine Etherbindung unter Verwendung eines Glutaraldehyd-Quervernetzungsmittels unter sauren Bedingungen gebildet wird.11. A process according to any one of claims 1 to 7, wherein an ether bond is formed using a glutaraldehyde crosslinking agent under acidic conditions. 12. Verfahren gemäß einem der Ansprüche 1 bis 11, wobei die Quervernetzung jedes Typs einer runktionellen Gruppe nacheinander bewirkt wird.12. A method according to any one of claims 1 to 11, wherein the crosslinking of each type of functional group is effected sequentially. 13. Verfahren gemäß Anspruch 12, das eine Quervernetzung von HA mit einem von HA verschiedenen Polymer über einer erste funktionelle Gruppe und anschließend weiter eine Quervernetzung des Produkts über eine zweite funktionelle Gruppe umfasst, wobei die besagten ersten und zweiten funktionellen Gruppen unterschiedlicher chemischer Natur sind.13. A process according to claim 12, which comprises cross-linking HA with a polymer other than HA via a first functional group and then further cross-linking the product via a second functional group, said first and second functional groups being of different chemical nature. 14. Verfahren gemäß Anspruch 13, wobei HA als erstes mit einem von HA verschiedenen Polymer über Hydroxylgruppen durch Bildung von Etherbindungen quervernetzt wird und anschließend entweder zu dem besagten Polymer oder einem anderen Molekül HA über Carboxylgruppen unter Bildung von Esterbindungen quervernetzt wird.14. A process according to claim 13, wherein HA is first cross-linked to a polymer other than HA via hydroxyl groups by forming ether bonds and is then cross-linked to either said polymer or another molecule of HA via carboxyl groups by forming ester bonds. SO 901 772.4 J · ···· · · J* · · · J · Q SO 901 772.4 J · ···· · · J* · · · J · Q Vitrolife LJK Ltd *· t .. »· ··**#» «JVitrolife LJK Ltd *· t .. »· ··**#» «J 2»' DE/EP 1 163274Tl2»' DE/EP 1 163274Tl 15. Verfahren gemäß einem der Ansprüche 1 bis 7 und 9 bis 11, wobei die Quervernetzung jedes Typs einer funktionellen Gruppe gleichzeitig bewirkt wird.15. A process according to any one of claims 1 to 7 and 9 to 11, wherein crosslinking of each type of functional group is effected simultaneously. 16. Verfahren gemäß einem der Ansprüche 1 bis 15 zur Herstellung von doppelt quervernetzter HA.16. Process according to one of claims 1 to 15 for the preparation of double cross-linked HA. 17. Verfahren gemäß Anspruch 16, das umfasst:17. A method according to claim 16, comprising: (a) eine Quervernetzung von HA mit einem zweiten Polymer über eine erste funktionelle Gruppe und anschließend(a) cross-linking HA with a second polymer via a first functional group and then (b) weiter eine Quervernetzung des Produkts aus (a) über eine zweite funktionelle Gruppe, wobei die besagten ersten und zweiten funktioneilen Gruppen unterschiedlicher chemischer Natur sind.(b) further cross-linking the product of (a) via a second functional group, wherein said first and second functional groups are of different chemical nature. 18. Mehrfach quervernetzte HA, die durch ein Verfahren gemäß einem der Ansprüche 1 bis 17 erhältlich ist.18. Multiply cross-linked HA obtainable by a process according to any one of claims 1 to 17. 19. HA, die mit einem oder mehreren von HA verschiedenen Polymeren quervernetzt ist, wobei die HA und das (die) besagte(n) Polymer(e) mit mindestens zwei verschiedenen Bindungstypen quervernetzt sind.19. HA cross-linked with one or more polymers other than HA, wherein the HA and said polymer(s) are cross-linked with at least two different bond types. 20. HA, die mit einem zweiten Polymer quervernetzt ist, wobei die HA und das besagte zweite Polymer durch zwei verschiedene Bindungstypen quervernetzt sind.20. HA cross-linked to a second polymer, wherein the HA and said second polymer are cross-linked by two different types of bonds. 21. HA, die mit einem von HA verschiedenen Polymer quervernetzt ist, wobei die HA mit dem besagten Polymer und mit einem anderen HA-Molekül durch mindestens zwei verschiedene Bindungstypen quervernetzt ist.21. HA cross-linked to a polymer other than HA, wherein the HA is cross-linked to the said polymer and to another HA molecule by at least two different types of bonds. 22. Quervemetzte HA gemäß einem der Ansprüche 18 bis 21, wobei die quervernetzenden Bindungen unter zwei oder mehr Ether-, Ester-, Sulfon-, Amin-, Imino- und Amidbindungen gewählt sind.22. Crosslinked HA according to any one of claims 18 to 21, wherein the crosslinking bonds are selected from two or more ether, ester, sulfone, amine, imino and amide bonds. 00901772.4 . · A 00901772.4 . · A Wrolife UK Ltd · .· * '.,'·.' «AL. 4Wrolife UK Ltd · .· * '.,'·.' «AL. 4 23. Mehrfach quervemetzte HA gemäß einem der Ansprüche 18 bis 22 in Form einer Folie. 23. Multiply cross-linked HA according to one of claims 18 to 22 in the form of a film. 24. Mehrfach quervemetzte HA gemäß einem der Ansprüche 18 bis 22 in Form eines Gels.24. Multiply cross-linked HA according to one of claims 18 to 22 in the form of a gel. 25. Produkt, umfassend eine mehrfach quervernetze HA gemäß einem der Ansprüche 18 bis 24.25. A product comprising a multiply cross-linked HA according to any one of claims 18 to 24. 26. Verwendung eines mehrfach quervemetzten HA-Derivats gemäß einem der Ansprüche 18 bis 24 bei der Herstellung eines Produkts für eine pharmazeutische, medizinische oder kosmetische Anwendung.26. Use of a multiply cross-linked HA derivative according to any one of claims 18 to 24 in the manufacture of a product for a pharmaceutical, medical or cosmetic application. 27. Verwendung eines mehrfach quervemetzten HA-Derivats gemäß einem der Ansprüche 18 bis 24 oder eines Produkts gemäß Anspruch 25 in der Medizin oder Chirurgie.27. Use of a multiply cross-linked HA derivative according to any one of claims 18 to 24 or of a product according to claim 25 in medicine or surgery.
DE1163274T 1999-02-05 2000-02-03 METHOD FOR CROSSLINKING HYALURONIC ACID WITH POLYMERS Pending DE1163274T1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9902652.8A GB9902652D0 (en) 1999-02-05 1999-02-05 Process
PCT/GB2000/000316 WO2000046252A1 (en) 1999-02-05 2000-02-03 Process for cross-linking hyaluronic acid to polymers

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DE1163274T1 true DE1163274T1 (en) 2002-11-14

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DE60029761T Expired - Lifetime DE60029761T2 (en) 1999-02-05 2000-02-03 METHOD OF NETWORKING HYALURONIC ACID WITH POLYMERS
DE1163274T Pending DE1163274T1 (en) 1999-02-05 2000-02-03 METHOD FOR CROSSLINKING HYALURONIC ACID WITH POLYMERS

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Country Status (16)

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US (2) US6703444B2 (en)
EP (1) EP1163274B9 (en)
JP (1) JP2002536465A (en)
CN (1) CN1243773C (en)
AT (1) ATE335011T1 (en)
AU (1) AU773628B2 (en)
BR (1) BR0007985B1 (en)
CA (1) CA2362233C (en)
DE (2) DE60029761T2 (en)
DK (1) DK1163274T3 (en)
ES (1) ES2181607T3 (en)
GB (1) GB9902652D0 (en)
MX (1) MXPA01007877A (en)
NZ (1) NZ512994A (en)
PT (1) PT1163274E (en)
WO (1) WO2000046252A1 (en)

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